One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition

Alejandro Islas-Jácome; Atilano Gutiérrez-Carrillo; Miguel A. García-Garibay; Eduardo González-Zamora

doi:10.1055/s-0033-1340218

Synlett, Table of Contents

Synlett 2014; 25(3): 403-406
DOI: 10.1055/s-0033-1340218

letter

One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition

Alejandro Islas-Jácome

^aDepartamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina Iztapalapa, C. P. 09340, México D. F., México Fax: +52(55)58044666 Email: egz@xanum.uam.mx

,

Atilano Gutiérrez-Carrillo

^aDepartamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina Iztapalapa, C. P. 09340, México D. F., México Fax: +52(55)58044666 Email: egz@xanum.uam.mx

,

Miguel A. García-Garibay

^bDepartment of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young, Drive East, Los Angeles, CA 90095-1569, USA

,

Eduardo González-Zamora*

^aDepartamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina Iztapalapa, C. P. 09340, México D. F., México Fax: +52(55)58044666 Email: egz@xanum.uam.mx

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Abstract

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Abstract

A rapid and efficient one-pot synthesis of a series of four novel nuevamine aza-analogues is described based on the oxidative Ugi-type reaction and aza-Diels–Alder reaction as post-functionalization. A simple IBX-mediated oxidation of a secondary amine followed by isonitrile α-addition and finally an aza-Diels–Alder cycloaddition provides the desired compounds in excellent overall yields considering the short reaction time, atom economy, and the molecular complexity of the final products. This protocol presents a highly attractive procedure for the rapid generation of fused polyheterocycles.

Key words

one-pot synthesis - natural products - oxidation - oxidative Ugi reaction - aza-Diels–Alder cycloaddition

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References

References and Notes

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